Title: Book the Best Hotels with POOL in Anna Maria Island in 2026 | Expedia.ca [Anna Maria Island Travel Guide](https://expedia.ca/Anna-Maria-Island.dx553248622847118534)[Hotels in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Hotels.d553248622847118534.Travel-Guide-Hotels)[Vacation Rentals in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Vacation-Rentals.d553248622847118534.Travel-Guide-VacationRentals)[Flights to Anna Maria Island](https://expedia.ca/Cheap-Flights-To-Anna-Maria-Island.d553248622847118534.Travel-Guide-Flights)[Things to do in Anna Maria Island](https://expedia.ca/Things-To-Do-In-Anna-Maria-Island.d553248622847118534.Travel-Guide-Activities)[Anna Maria Island Car Rentals](https://expedia.ca/Car-Rentals-In-Anna-Maria-Island.d553248622847118534.Car-Rental-Guide)[Anna Maria Island Vacation Packages](https://expedia.ca/Anna-Maria-Island.d553248622847118534.Destination-Travel-Guides) ![Anna Maria Island, FL Pier ](https://images.trvl-media.com/place/553248622847118534/f6726703-de53-4942-875e-504e17e1a1f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Anna Maria Island, FL from CA $242 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Anna Maria Island Hotels with a Pool Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-11&endDate=2025-12-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Anna Maria Island hotels with a pool ![Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/efe82ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/fc900ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 Bedroom Queen Suite](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/1dc05c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room | Garden view](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/222a0692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Haley's at The Anna Maria Island Inn [](https://www.expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information) Holmes Beach 8.6/10 Excellent (399) "Beautiful location. Walking distance to beach. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $191 CA $242 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/519687a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/32e3bf8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/da8fadd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/bdd0449e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze at Anna Maria Island Inn [](https://www.expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) Bradenton Beach 8.8/10 Excellent (56) "Nice Place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rafael CA $248 CA $313 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/c4463db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, white sand](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/0d4c4896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/1b0e5d4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Condo](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/79258cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alamanda Villas [](https://www.expedia.ca/Holmes-Beach-Hotels-Alamanda-Villas.h120114144.Hotel-Information) Holmes Beach 10/10 Exceptional (3) "The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci CA $316 CA $634 total includes taxes & fees Dec 12 - Dec 13 [](https://www.expedia.ca/Holmes-Beach-Hotels-Alamanda-Villas.h120114144.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/651a8200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/85b3dcb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/5f1d6b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/961f9fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Quarters at Anna Maria Island Inn [](https://www.expedia.ca/Sarasota-Hotels-Captains-Quarters-By-AMI-Locals.h59789467.Hotel-Information) Bradenton Beach 9.4/10 Exceptional (22) "Very clean new place great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $570 CA $722 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Sarasota-Hotels-Captains-Quarters-By-AMI-Locals.h59789467.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/0ce71205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/b209e6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/e64ffac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Island | View from room](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/e4cee807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Retreat at Anna Maria Island Inn [](https://www.expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.Hotel-Information) Bradenton Beach 9.4/10 Exceptional (35) "Beautiful room, convenient location, and excellent service! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bianca CA $521 CA $660 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/23e5431b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/4caa2fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Villa, 2 Bedrooms, Non Smoking, Garden View | Private kitchen](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/91866373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/def997fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm Tree Villas [](https://www.expedia.ca/Sarasota-Hotels-Palm-Tree-Villas.h5411119.Hotel-Information) Holmes Beach 9.2/10 Wonderful (172) "We had a great stay! The property was located within a short walk to the beach. We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Sarasota-Hotels-Palm-Tree-Villas.h5411119.Hotel-Information) ![The Anna Maria Luxury Suite | View from room](https://images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/e540b881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Luxury 1 Bedroom King Suite | Living area](https://images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/f0fa24c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, white sand, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/aebd1d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront 1 Bedroom King Suite | View from room](https://images.trvl-media.com/lodging/74000000/73260000/73251000/73250924/d857bfd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Resort [](https://www.expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.Hotel-Information) Holmes Beach 9.4/10 Exceptional (289) "Beautiful resort, stunning setting, amazing beach access and spotless everywhere. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Kimberley CA $486 CA $616 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Holmes-Beach-Hotels-Anna-Maria-Beach-Resort.h73250924.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/ce1b2724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 Bedroom King Suite | Living area](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/9c445d8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/4174e2ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/2d6f0d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelican Post at Anna Maria Island Inn [](https://www.expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) Bradenton Beach 9.2/10 Wonderful (328) "Fabulous stay! Super clean!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $459 CA $582 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/933a3ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/b018f64f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/19ccb378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/ebba9faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand! [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.Hotel-Information) Anna Maria 9.8/10 Exceptional (36) "Location was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. CA $273 CA $709 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/ed3fe6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/6b536dc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/0d3bae69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/41000000/40290000/40281600/40281514/716bb273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Bungalow with Pool and Bay Views! [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Bungalow-With-Pool-And-Bay-Views-Barefoot-By-The-Bay-At-Bayside-Bun.h40281514.Hotel-Information) Anna Maria 9.8/10 Exceptional (37) "Great location,great property,spacious,clean everything brand new in the property,beach across the street,my family love it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michel CA $239 CA $543 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Bungalow-With-Pool-And-Bay-Views-Barefoot-By-The-Bay-At-Bayside-Bun.h40281514.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26®ionId=553248622847118534&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Anna Maria Island Hotel Reviews ![Haley's at The Anna Maria Island Inn](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/fc900ac2_y.jpg) ### Haley's at The Anna Maria Island Inn 10/10 Excellent "Beautiful location. Walking distance to beach. " [](https://expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information) ![Silver Surf Gulf Beach Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045895/12fa4f1f_y.jpg) ### Silver Surf Gulf Beach Resort 10/10 Excellent "Our room was immaculate and facilities are clean and maintained. The staff was incredibly nice and we will definitely be returning." [](https://expedia.ca/Sarasota-Hotels-Silver-Surf-Gulf-Beach-Resort.h1045895.Hotel-Information) ![Bridgewalk Resort](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "The rooms are extremely nice and very clean. Every staff member that we encountered during our stay was super friendly. The location is perfect and within walking distance from just about anything you need. The beach is about 100 yards away from the location. We will definitely be back!!!" [](https://expedia.ca/Sarasota-Hotels-Bridgewalk-A-Landmark-Resort.h1045894.Hotel-Information) ![Tortuga Inn Beach Resort](https://images.trvl-media.com/lodging/2000000/1060000/1054200/1054101/b1d10d73_y.jpg) ### Tortuga Inn Beach Resort 10/10 Excellent "The room was absolutely spotless. It was perfect for the 2 of us. This resort is smack dab in the middle of everything and the staff is top notch. We couldn't have asked for a better stay. We'll be coming back year after year! " [](https://expedia.ca/Sarasota-Hotels-Tortuga-Inn-Beach-Resort.h1054101.Hotel-Information) ![Seabreeze at Anna Maria Island Inn](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/a71dc126_y.jpg) ### Seabreeze at Anna Maria Island Inn 10/10 Excellent "Balcony was great! It was wonderful to be able to walk right out on the beach instead of having to drive and find a parking spot. " [](https://expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) ![Palm Tree Villas](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/def997fa_y.jpg) ### Palm Tree Villas 10/10 Excellent "We had a great stay! The property was located within a short walk to the beach. We will be back!" [](https://expedia.ca/Sarasota-Hotels-Palm-Tree-Villas.h5411119.Hotel-Information) ![Waterline Villas & Marina, Autograph Collection](https://images.trvl-media.com/lodging/16000000/15740000/15739500/15739491/c50d8ef8_y.jpg) ### Waterline Villas & Marina, Autograph Collection 10/10 Excellent "Exceptional " [](https://expedia.ca/Sarasota-Hotels-Waterline-Marina-Resort-Beach-Club.h15739491.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Anna Maria ](https://www.expedia.ca/Anna-Maria-Hotels-Adults-Only-Resorts.0-0-d74028-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Anna Maria ](https://www.expedia.ca/Anna-Maria-Hotels-All-Inclusive-Hotel.0-0-d74028-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Anna Maria ](https://www.expedia.ca/Anna-Maria-Hotels-Beach-Hotel.0-0-d74028-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Anna Maria ](https://www.expedia.ca/Anna-Maria-Hotels-Boutique-Hotel.0-0-d74028-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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